Tetrahydrofuran → HCID 13662753, compound

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Reaction Steps

To 100 ml. of a solution of diborane in tetrahydrofuran (0.93 molar, 0.093 mole) was added a solution of 9.0 g. (0.033 mole) of the above-prepared propionamide. The mixture was refluxed overnight, cooled and methanol added to destroy unreacted diborane. Ethereal hydrogen chloride and methanol were added and the mixture evaporated to dryness. The residue was dissolved in dilute hydrochloric acid/ether and the acidic aqueous solution was basified, extracted with ether and the dried ether extract evaporated to yield N-(n-propyl)-2-chloro-3,4-dimethoxyphenethylamine. The latter (3.5 g., 0.0137 mole) was dissolved in 100 ml. of propionic anhydride and stirred overnight. The mixture was evaporated nearly to dryness, toluene was added and then further evaporated to leave N-(2-chloro-3,4-dimethoxyphenethyl)-N-(n-propyl)propionamide.

Provenance & Evidence